bis(phenylmethyl) (1α,2α,4β,5β)-(4,5-dihydroxy-1,2-cyclohexanediyl)bis(carbamate) | 478856-68-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: bis(phenylmethyl) (1α,2α,4β,5β)-(4,5-dihydroxy-1,2-cyclohexanediyl)bis(carbamate)
• 英文别名: benzyl N-[(1S,2R,4R,5S)-4,5-dihydroxy-2-(phenylmethoxycarbonylamino)cyclohexyl]carbamate
• CAS: 478856-68-7
• 化学式: C₂₂H₂₆N₂O₆
• 分子量: 414.458
• InChiKey: CPQTYBZZEATNJN-FGYAAKKASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  30
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  117
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  bis(phenylmethyl) (1α,2α,4β,5β)-(4,5-dihydroxy-1,2-cyclohexanediyl)bis(carbamate) 在 palladium on activated charcoal 1,2,2,6,6-五甲基哌啶 、 氢气 、 sodium hydride 、 对甲苯磺酸 作用下， 以 1,4-二氧六环 、 甲醇 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， -70.0~75.0 ℃ 、137.9 kPa 条件下， 反应 26.67h， 生成 (3aα,5α,6α,7aα)-4,4'-(hexahydro-2,2-dimethyl-1,3-benzodioxole-5,6-diyl)bis(2,6-piperazinedione)
  参考文献：
  名称：

  Syntheses and proton NMR conformational analyses of diastereomeric 4,4'-(4,5-dihydroxy-1,2-cyclohexanediyl)bis(2,6-piperazinedione)s and a synthetically related tricyclic octahydro-2,2-dimethyl-6-oxo-1,3-dioxolo[4,5-g]quinoxaline-5,8-diacetic acid ester

  摘要：

  Efficient syntheses for five of the six possible diastereoisomeric 4,4'-(4,5-dihydroxy-1,2-cyclohexanediyl)bis-(2,6-dioxopiperazine)s (5-9) and a synthetically related tricyclic 1,3-dioxolo[4,5-g]quinoxaline ring system 45 from their respective (4,5-dihydroxy-1,2-cyclohexanediyl)bis(carbamate)s 11-16 via isopropylidene-protected intermediates are described. Solution conformations of all targets and several synthetic intermediates in DMSO-d6 were determined using H-1 NMR and NOE methods, and the structure for polyheterocycle 45, obtained during attempted preparation of the sixth possible dioxopiperazine diastereomer 10, was determined with the additional aid of 2D COSY, 2D HETCOR, and H-1-C-13 correlation of long-range coupling (COLOC). Taken together, these studies provide evidence for the differences in reaction conditions required for bis(dioxopiperazine) synthesis, a relatively comprehensive analysis of dioxopiperazine and hydroxyl substituent effects on cyclohexane DMSO-d6 solution conformations, and a preliminary analysis of aqueous solubility differences.

  DOI：

  10.1021/jo00018a039
• 作为产物：
  描述：

  bis(phenylmethyl) (1α,2α-cyclohexanediyl)bis(carbamate) 在 四氧化锇 、 水 、 N-甲基吗啉氧化物 、 叔丁醇 作用下， 以 四氯化碳 、 丙酮 为溶剂， 反应 16.0h， 以52%的产率得到bis(phenylmethyl) (1α,2α,4β,5β)-(4,5-dihydroxy-1,2-cyclohexanediyl)bis(carbamate)
  参考文献：
  名称：

  立体控制合成的六个非对映异构体1,2-二羟基-4,5-二氨基环己烷：PtII配合物和P-388抗肿瘤特性。

  摘要：

  描述了由环己烯二胺cis-4和trans-5的六个非对映异构体1,2-二羟基-4,5-二氨基环己烷3a-f的立体控制的合成。Cbz保护的物种cis-9和trans-11分别作为这些环己二醇二胺（CDD）稳定的Cbz保护的前体的来源，这些环氧化物在催化（H2，Pd / C）氢化后释放。9的催化渗透作用提供了非对映二醇13和14的混合物，它们分别用作顺式-抗-顺式CDD 3b和顺式-顺式-顺式CDD 3a的前体，而11的渗透作用产生了预期的单一产物12顺-反-反CDD 3d。烯烃9和11的环氧化分别提供了环氧乙烷15和17，它们在酸催化水解后产生了相应的Cbz保护的二醇16和18，它是CDD反-反-顺3c和反-反-反3e的前体。由环氧乙烷17形成二醇18的同时伴随有2-oxa-4-氮杂双环[3.3.1]壬基3-one 19的形成。CDD反式-反式-反式3f是由二醇12通过区域选择性单乙酰化制备

  DOI：

  10.1021/jm00391a011

文献信息

• Ethylenediamine derivatives
  申请人：——

  公开号：US20040122063A1

  公开（公告）日：2004-06-24

  The invention relates a compound represented by the formula (1): Q 1 -Q 2 -C(═O)—N(R 1 )-Q 3 -N(R 2 )-T 1 -Q 4 ( 1 ) wherein R 1 and R 2 represent H or the like; Q 1 represents an aromatic ring, heterocyclic ring or the like; Q 2 represents a single bond, aromatic ring, heterocyclic ring or the like; Q 3 represents a group 1 or the like, Q 4 represents an aromatic ring, heterocyclic ring or the like; and T 1 represents —CO— or —SO 2 —, and a medicine which comprises the compound and is useful for thrombosis and embolism.

  本发明涉及一种由式（1）表示的化合物：Q1-Q2-C(═O)—N(R1)-Q3-N(R2)-T1-Q4(1)，其中R1和R2代表H或类似物；Q1代表芳香环，杂环或类似物；Q2代表单键，芳香环，杂环或类似物；Q3代表群1或类似物，Q4代表芳香环，杂环或类似物；T1代表—CO—或—SO2—，以及包含该化合物并对治疗血栓和栓塞有用的药物。
• Noncovalent Secondary Interactions in Co(II)Salen Complexes:  O₂ Binding and Catalytic Activity in Cyclohexene Oxygenation
  作者：Roberto Fiammengo、Christiaan M. Bruinink、Mercedes Crego-Calama、David N. Reinhoudt

  DOI：10.1021/jo026118a

  日期：2002.11.1

  The O-2 affinity of Co(II)Salen complexes 1-4 and their reactivity in cyclohexene oxygenation reactions of Co(II)Salen complexes 1-4 are modulated by noncovalent interactions such as hydrogen bonding and steric hindrance using a functionalized diamino bridge. Higher O-2 affinity is observed in the case of efficient hydrogen-bonding interactions (complex 1), while increased steric hindrance (cis vs trans diamino bridge) around the Co-coordinated O-2 is influencing the reactivity of the complexes.
• ETHYLENEDIAMINE DERIVATIVES
  申请人：Daiichi Sankyo Company, Limited

  公开号：EP1270557B1

  公开（公告）日：2012-07-25
• WITIAK, DONALD T.;ROTELLA, DAVID P.;FILPPI, JOYCE A.;GALLUCII, JUDITH, J. MED. CHEM., 30,(1987) N 8, 1327-1336
  作者：WITIAK, DONALD T.、ROTELLA, DAVID P.、FILPPI, JOYCE A.、GALLUCII, JUDITH

  DOI：——

  日期：——
• Monoacylated 1,2-diaminocycloalkanes
  申请人：Daiichi Sankyo Company, Limited

  公开号：EP2431370B1

  公开（公告）日：2013-06-19